diff --git a/.github/workflows/TestCITools.yml b/.github/workflows/TestCITools.yml
index cf79c241..b70366fe 100644
--- a/.github/workflows/TestCITools.yml
+++ b/.github/workflows/TestCITools.yml
@@ -39,6 +39,7 @@ jobs:
       # mingw arch below is not opt-in, included to check that it is allowed in the list
       opt_in_archs: 'windows_arm64;windows_amd64_mingw;'
       save_cache: ${{ github.event_name != 'pull_request' }}
+      vcpkg_triplets_override: 'windows_arm64:arm64-windows-static-md-release-vs2019comp;'
 
   extension-template-main:
     name: Extension template
diff --git a/.github/workflows/_extension_distribution.yml b/.github/workflows/_extension_distribution.yml
index 08811ca2..32676142 100644
--- a/.github/workflows/_extension_distribution.yml
+++ b/.github/workflows/_extension_distribution.yml
@@ -72,6 +72,11 @@ on:
         required: false
         type: string
         default: ''
+      # format: 'arch_name1:triplet1;arch_name2:triplet2'
+      vcpkg_triplets_override:
+        required: false
+        type: string
+        default: ''
       # Override the default script producing the matrices. Allows specifying custom matrices.
       matrix_parse_script:
         required: false
@@ -200,10 +205,42 @@ jobs:
       - id: parse-matrices
         run: |
           mkdir build
-          python3 ${{ inputs.matrix_parse_script }} --input extension-ci-tools/config/distribution_matrix.json --select_os linux   --output build/linux_matrix.json   --exclude "${{ inputs.exclude_archs }}" --opt_in "${{ inputs.opt_in_archs }}" --pretty --reduced_ci_mode ${{ inputs.reduced_ci_mode }}
-          python3 ${{ inputs.matrix_parse_script }} --input extension-ci-tools/config/distribution_matrix.json --select_os osx     --output build/osx_matrix.json     --exclude "${{ inputs.exclude_archs }}" --opt_in "${{ inputs.opt_in_archs }}" --pretty --reduced_ci_mode ${{ inputs.reduced_ci_mode }}
-          python3 ${{ inputs.matrix_parse_script }} --input extension-ci-tools/config/distribution_matrix.json --select_os windows --output build/windows_matrix.json --exclude "${{ inputs.exclude_archs }}" --opt_in "${{ inputs.opt_in_archs }}" --pretty --reduced_ci_mode ${{ inputs.reduced_ci_mode }}
-          python3 ${{ inputs.matrix_parse_script }} --input extension-ci-tools/config/distribution_matrix.json --select_os wasm    --output build/wasm_matrix.json    --exclude "${{ inputs.exclude_archs }}" --opt_in "${{ inputs.opt_in_archs }}" --pretty --reduced_ci_mode ${{ inputs.reduced_ci_mode }}
+          python3 ${{ inputs.matrix_parse_script }}                    \
+            --input extension-ci-tools/config/distribution_matrix.json \
+            --select_os linux                                          \
+            --output build/linux_matrix.json                           \
+            --exclude "${{ inputs.exclude_archs }}"                    \
+            --opt_in "${{ inputs.opt_in_archs }}"                      \
+            --pretty                                                   \
+            --reduced_ci_mode ${{ inputs.reduced_ci_mode }}            \
+            --vcpkg_triplets_override "${{ inputs.vcpkg_triplets_override }}"
+          python3 ${{ inputs.matrix_parse_script }}                    \
+            --input extension-ci-tools/config/distribution_matrix.json \
+            --select_os osx                                            \
+            --output build/osx_matrix.json                             \
+            --exclude "${{ inputs.exclude_archs }}"                    \
+            --opt_in "${{ inputs.opt_in_archs }}"                      \
+            --pretty                                                   \
+            --reduced_ci_mode ${{ inputs.reduced_ci_mode }}            \
+            --vcpkg_triplets_override "${{ inputs.vcpkg_triplets_override }}"
+          python3 ${{ inputs.matrix_parse_script }}                    \
+            --input extension-ci-tools/config/distribution_matrix.json \
+            --select_os windows                                        \
+            --output build/windows_matrix.json                         \
+            --exclude "${{ inputs.exclude_archs }}"                    \
+            --opt_in "${{ inputs.opt_in_archs }}"                      \
+            --pretty                                                   \
+            --reduced_ci_mode ${{ inputs.reduced_ci_mode }}            \
+            --vcpkg_triplets_override "${{ inputs.vcpkg_triplets_override }}"
+          python3 ${{ inputs.matrix_parse_script }}                    \
+            --input extension-ci-tools/config/distribution_matrix.json \
+            --select_os wasm                                           \
+            --output build/wasm_matrix.json                            \
+            --exclude "${{ inputs.exclude_archs }}"                    \
+            --opt_in "${{ inputs.opt_in_archs }}"                      \
+            --pretty                                                   \
+            --reduced_ci_mode ${{ inputs.reduced_ci_mode }}            \
+            --vcpkg_triplets_override "${{ inputs.vcpkg_triplets_override }}"
 
       - id: set-matrix-linux
         run: |
diff --git a/makefiles/c_api_extensions/base.Makefile b/makefiles/c_api_extensions/base.Makefile
index cd4e9508..e952217e 100644
--- a/makefiles/c_api_extensions/base.Makefile
+++ b/makefiles/c_api_extensions/base.Makefile
@@ -39,6 +39,13 @@ ifeq ($(DUCKDB_PLATFORM),windows_amd64_mingw)
 	EXTENSION_LIB_FILENAME=lib$(EXTENSION_NAME).dll
 endif
 
+# Propagate toolchains
+ifeq ($(DUCKDB_PLATFORM),windows_amd64)
+       TOOLCHAIN_FLAGS:=${TOOLCHAIN_FLAGS} -DVCPKG_OVERLAY_TRIPLETS=${PROJ_DIR}extension-ci-tools/toolchains/
+else ifeq ($(DUCKDB_PLATFORM),windows_arm64)
+       TOOLCHAIN_FLAGS:=${TOOLCHAIN_FLAGS} -DVCPKG_OVERLAY_TRIPLETS=${PROJ_DIR}extension-ci-tools/toolchains/
+endif
+
 #############################################
 ### Main extension parameters
 #############################################
diff --git a/makefiles/duckdb_extension.Makefile b/makefiles/duckdb_extension.Makefile
index b65eb6a6..6f921aaf 100644
--- a/makefiles/duckdb_extension.Makefile
+++ b/makefiles/duckdb_extension.Makefile
@@ -97,6 +97,12 @@ ifneq ("${VCPKG_HOST_TRIPLET}", "")
 	TOOLCHAIN_FLAGS:=${TOOLCHAIN_FLAGS} -DVCPKG_HOST_TRIPLET='${VCPKG_HOST_TRIPLET}'
 endif
 
+ifeq ($(DUCKDB_PLATFORM),windows_amd64)
+	TOOLCHAIN_FLAGS:=${TOOLCHAIN_FLAGS} -DVCPKG_OVERLAY_TRIPLETS=${PROJ_DIR}extension-ci-tools/toolchains/
+else ifeq ($(DUCKDB_PLATFORM),windows_arm64)
+	TOOLCHAIN_FLAGS:=${TOOLCHAIN_FLAGS} -DVCPKG_OVERLAY_TRIPLETS=${PROJ_DIR}extension-ci-tools/toolchains/
+endif
+
 #### Enable Ninja as generator
 ifeq ($(GEN),ninja)
 	GENERATOR=-G "Ninja" -DFORCE_COLORED_OUTPUT=1
diff --git a/scripts/modify_distribution_matrix.py b/scripts/modify_distribution_matrix.py
index 09c2c2cb..1003c23a 100644
--- a/scripts/modify_distribution_matrix.py
+++ b/scripts/modify_distribution_matrix.py
@@ -15,6 +15,7 @@
 parser.add_argument("--reduced_ci_mode", required=True, help="Set to default/enabled/disabled, when enabled, filters out redundant archs for testing")
 parser.add_argument("--select_os", help="Select an OS to include in the output JSON")
 parser.add_argument("--deploy_matrix", action="store_true", help="Create a merged list used in deploy step")
+parser.add_argument("--vcpkg_triplets_override", required=False, default="", help="Format: 'arch_name1:triplet1;arch_name2:triplet2'")
 args = parser.parse_args()
 
 
@@ -39,6 +40,19 @@
 else:
     raise Exception("Unknown reduced_ci_mode value: " + reduced_ci_mode + " - must be auto/enabled/disabled.")
 
+# Parse VCPKG triplets override
+triplet_pairs = args.vcpkg_triplets_override.split(";")
+triplet_dict = {}
+for pair in triplet_pairs:
+    stripped = pair.strip()
+    if len(stripped) == 0:
+        continue
+    parts = stripped.split(":")
+    if len(parts) != 2:
+        raise Exception(f"Invalid 'vcpkg_triplets_override' entry: {stripped},\
+ must be in format: 'arch_name1:triplet1'")
+    triplet_dict[parts[0]] = parts[1]
+
 # Read the input JSON file
 with open(input_json_file_path, "r") as json_file:
     data = json.load(json_file)
@@ -58,6 +72,14 @@ def filter_entries(data, excluded_arch_values, opt_in_arch_values):
     for os, config in data.items():
         if "include" in config:
             config["include"] = [entry for entry in config["include"] if should_run(entry, reduced_ci_mode, excluded_arch_values, opt_in_arch_values)]
+
+            # Override VCPKG triplets
+            for entry in config["include"]:
+                override = triplet_dict.get(entry["duckdb_arch"])
+                if override is not None:
+                    entry["vcpkg_target_triplet"] = override
+                    entry["vcpkg_host_triplet"] = override
+
         if not config["include"]:
             del config["include"]
 
@@ -67,6 +89,7 @@ def filter_entries(data, excluded_arch_values, opt_in_arch_values):
 # Filter the JSON data
 filtered_data = filter_entries(data, excluded_arch_values, opt_in_arch_values)
 
+
 # Select an OS if specified
 if select_os:
     found = False
diff --git a/toolchains/arm64-windows-static-md-release-vs2019comp.cmake b/toolchains/arm64-windows-static-md-release-vs2019comp.cmake
new file mode 100644
index 00000000..5343db8b
--- /dev/null
+++ b/toolchains/arm64-windows-static-md-release-vs2019comp.cmake
@@ -0,0 +1,11 @@
+# It is necessary to pass this flag to AWS C++ SDK to enable compatibility with VS2019 C++ stdlib
+set(VCPKG_CXX_FLAGS "/D_DISABLE_CONSTEXPR_MUTEX_CONSTRUCTOR")
+# If VCPKG_CXX_FLAGS is set, VCPKG_C_FLAGS must be set
+set(VCPKG_C_FLAGS "")
+
+# The following is copied from arm64-windows-static-md-release.cmake
+set(VCPKG_TARGET_ARCHITECTURE arm64)
+set(VCPKG_CRT_LINKAGE dynamic)
+set(VCPKG_LIBRARY_LINKAGE static)
+
+set(VCPKG_BUILD_TYPE release)
diff --git a/toolchains/x64-windows-static-md-release-vs2019comp.cmake b/toolchains/x64-windows-static-md-release-vs2019comp.cmake
new file mode 100644
index 00000000..7970c1f7
--- /dev/null
+++ b/toolchains/x64-windows-static-md-release-vs2019comp.cmake
@@ -0,0 +1,11 @@
+# It is necessary to pass this flag to AWS C++ SDK to enable compatibility with VS2019 C++ stdlib
+set(VCPKG_CXX_FLAGS "/D_DISABLE_CONSTEXPR_MUTEX_CONSTRUCTOR")
+# If VCPKG_CXX_FLAGS is set, VCPKG_C_FLAGS must be set
+set(VCPKG_C_FLAGS "")
+
+# The following is copied from x64-windows-static-md-release.cmake
+set(VCPKG_TARGET_ARCHITECTURE x64)
+set(VCPKG_CRT_LINKAGE dynamic)
+set(VCPKG_LIBRARY_LINKAGE static)
+
+set(VCPKG_BUILD_TYPE release)